ethyl 2-(quinolin-4-ylamino)benzoate | 1111618-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 2-(quinolin-4-ylamino)benzoate
• CAS: 1111618-69-9
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: PLUIHZYJNKCANN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(quinolin-4-ylamino)benzoate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以88%的产率得到2-quinolin-4-ylamino-benzoic acid
  参考文献：
  名称：

  Selective Non-nucleoside Inhibitors of Human DNA Methyltransferases Active in Cancer Including in Cancer Stem Cells

  摘要：

  DNA methyltransferases (DNMTs) are important enzymes involved in epigenetic control of gene expression and represent valuable targets in cancer chemotherapy. A number of nucleoside DNMT inhibitors (DNMTi) have been studied in cancer, including in cancer stem cells, and two of them (azacytidine and decitabine) have been approved for treatment of myelodysplastic syndromes. However, only a few non-nucleoside DNMTi have been identified so far, and even fewer have been validated in cancer. Through a process of hit-to-lead optimization, we report here the discovery of compound 5 as a potent non-nucleoside DNMTi that is also selective toward other Ado Met-dependent protein methyltransferases. Compound 5 was potent at single-digit micromolar concentrations against a panel of cancer cells and was less toxic in peripheral blood mononuclear cells than two other compounds tested. In mouse medulloblastoma stem cells, 5 inhibited cell growth, whereas related compound 2 showed high cell differentiation. To the best of our knowledge, 2 and 5 are the first non-nucleoside DNMTi tested in a cancer stem cell line.

  DOI：

  10.1021/jm4012627
• 作为产物：
  描述：

  4-氯喹啉 、 2-氨基苯甲酸乙酯 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 17.0h， 以81%的产率得到ethyl 2-(quinolin-4-ylamino)benzoate
  参考文献：
  名称：

  自动串联催化：通过钯催化的分子间CN和分子内CC键的形成合成11 H-吲哚并[3,2- c ]喹啉

  摘要：

  D-Ring取代的11 H-吲哚并[3,2- c ]喹啉（4）是通过自动串联连续分子间Buchwald-Hartwig反应和分子内钯催化的4-氯喹啉（1）上的N-未取代的2芳基化反应制得的-氯苯胺（2）。报道的11 H-吲哚并[3,2- c ]喹啉（4）代表了第一个实例，其中串联催化已用于构建N-未取代的咔啉。

  DOI：

  10.1002/adsc.200700328